Water → 2-(Pyridin-2-yl)pyrimidine-5-carboxylic acid-(4-fluoroindol-1-yl)amide

HRID 2381938Notes

Reaction equation

HRID 2381938 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:12]=[CH:11][C:10]([C:13](Cl)=[O:14])=[CH:9][N:8]=1.[NH2:16][N:17]1[C:25]2[C:20](=[C:21]([F:26])[CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18]1.C([O-])([O-])=O.[K+].[K+].O>CCOC(C)=O>[F:26][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:20]=1[CH:19]=[CH:18][N:17]2[NH:16][C:13]([C:10]1[CH:9]=[N:8][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:12][CH:11]=1)=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 68553171HCID 68553171, compoundHCID 86639367HCID 86639367, compound

Product 1

HCID 250996582-(Pyridin-2-yl)pyrimidine-5-carboxylic acid-(4-fluoroindol-1-yl)amideYield 17.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A suspension of 2-(pyridine-2-yl)-pyrimidine-5-carbonyl chloride (0.44 g) in EtOAc (20 mL) is added portion wise to a mixture of 1-amino-4-fluoroindole (0.30 g) and K2CO3 (0.276 g) in EtOAc (10 mL)/water (20 mL) and the resulting mixture is stirred at rt for 24 h. The aqueous phase is separated and extracted twice with EtOAc. The combined organic layer is washed with water and brine, dried (MgSO4), filtered and concentration in vacuo. The residue is purified by silica gel chromatography eluting with EtOAc to afford 2-(pyridin-2-yl)pyrimidine-5-carboxylic acid-(4-fluoroindol-1-yl)amide (0.115 g, 17%) as a solid. MS: 334 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 6.65 (d, 1H), 6.89-6.95 (q, 1H), 7.16-7.23 (m, 1H), 7.32-7.35 (d, 1H), 7.57 (d, 1H), 7.57-7.64 (m, 1H), 8.02-8.08 (t, 1H), 8.50-8.52 (d, 1H), 8.82-8.83 (d, 1H), 9.49 (s, 2H), 12.30 (s, 1H).

Workup

  1. additionis added portion
  2. customThe aqueous phase is separated
  3. extractionextracted twice with EtOAc
  4. washThe combined organic layer is washed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentration in vacuo
  8. customThe residue is purified by silica gel chromatography
  9. washeluting with EtOAc

Sources & evidence

ORD record
ord-c687b198df5143e996952f0e5c03122c
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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